反応 #45865

反応方程式

Imidazole

triphenyl phosphine

iodine

2-cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

sodium thiosulfate

→

compound

収率 80.3%

2-Cyclopropyl-7-(1-iodomethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

収率 80.3%

溶媒

benzene

反応条件

後処理

1. 1
   workup.STIRRINGby stirring at the same temperature for 10 minutes
2. 2
   その他The aqueous layer was separated
3. 3
   抽出this was extracted three times with ethyl acetate
4. 4
   洗浄washed with saturated brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   その他The insoluble matter was separated by filtration
7. 7
   その他the solvent was evaporated away
8. 8
   その他the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

実験手順

Imidazole (321 mg, 4.71 mmol), triphenyl phosphine (1.235 g, 4.71 mmol) and then iodine (956 mg, 3.77 mmol) were added to a solution of 2-cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-297) (675 mg, 1.88 mmol) dissolved in benzene (20 ml). The solution was stirred under nitrogen atmosphere at room temperature for 20 hours, then aqueous saturated sodium thiosulfate solution was added, followed by stirring at the same temperature for 10 minutes. The aqueous layer was separated, this was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=19:1, v/v) to obtain the entitled compound (707 mg, 80%).

出典